N,N'-Bis(2,2,3,3,4,4,4-hepta-fluoro-butyl)naphthalene-1,4:5,8-tetra-carboximide.

The title mol-ecule, C(22)H(8)F(14)N(2)O(4), lies across a crystallographic inversion center with the naphthalene diimide core essentially planar (mean deviation from plane is 0.0583 Å). The CF(2) groups in the perfluorobutyl chains are in an energetically favorable all trans conformation. In the crystal structure, mol-ecules are packed in slightly displaced layers so that the side chains overlap the aromatic naphthalene diimide rings, thus minimizing any possible π-π overlap.

Related literature

For general background on the semic-conducting properties and use of this class of materials in organic thin-film transistor applications, see: Chesterfield et al. (2004a ▶,b ▶); Facceti et al. (2008 ▶); Jones et al. (2004 ▶); Katz et al. (2000a ▶,b ▶); Kazmaier & Hoffmann (1994 ▶); Klebe et al. (1989 ▶); Shukla et al. (2008 ▶); Wurthner (2004 ▶).

Experimental

Crystal data

C22H8F14N2O4

M = 630.30

Triclinic,

a = 5.1910 (5) Å

b = 10.1459 (12) Å

c = 11.5988 (15) Å

α = 66.693 (4)°

β = 79.064 (4)°

γ = 89.115 (7)°

V = 549.64 (11) Å3

Z = 1

Mo Kα radiation

μ = 0.21 mm−1

T = 293 (2) K

0.15 × 0.10 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

3049 measured reflections

2094 independent reflections

909 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.223

S = 0.93

2094 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Materials Studio (Accelrys, 2002 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036738/lh2728sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036738/lh2728Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H8F14N2O4	Z = 1
Mr = 630.30	F000 = 312
Triclinic, P1	Dx = 1.904 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.1910 (5) Å	Cell parameters from 4558 reflections
b = 10.1459 (12) Å	θ = 1.0–26.7º
c = 11.5988 (15) Å	µ = 0.21 mm−1
α = 66.693 (4)º	T = 293 (2) K
β = 79.064 (4)º	Needle, pink
γ = 89.115 (7)º	0.15 × 0.10 × 0.05 mm
V = 549.64 (11) Å3

Nonius KappaCCD diffractometer	2094 independent reflections
Radiation source: fine-focus sealed tube	909 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.057
Detector resolution: 9 pixels mm-1	θmax = 26.6º
T = 293(2) K	θmin = 4.1º
φ and ω scans	h = −6→6
Absorption correction: none	k = −12→11
3049 measured reflections	l = −14→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.223	w = 1/[σ2(Fo2) + (0.1P)2 + 0.3623P] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
2094 reflections	Δρmax = 0.23 e Å−3
190 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
F1	0.1050 (6)	0.4145 (3)	0.7561 (3)	0.0814 (11)
F2	0.1713 (6)	0.5174 (3)	0.8788 (3)	0.0828 (12)
F3	0.5849 (6)	0.3623 (4)	0.9393 (3)	0.0873 (12)
F4	0.5572 (7)	0.2684 (3)	0.8049 (3)	0.0883 (12)
F5	0.3622 (7)	0.0974 (4)	1.0537 (3)	0.0931 (12)
F6	0.0806 (7)	0.2472 (4)	1.0654 (4)	0.1050 (15)
F7	0.0800 (9)	0.1477 (4)	0.9346 (4)	0.1234 (17)
O1	0.2493 (8)	0.6081 (4)	0.4924 (4)	0.0742 (12)
O2	0.5194 (8)	0.8024 (4)	0.7439 (4)	0.0725 (12)
N1	0.3566 (7)	0.6967 (4)	0.6298 (4)	0.0484 (11)
C1	0.2325 (10)	0.7037 (5)	0.5308 (5)	0.0528 (14)
C2	0.0799 (9)	0.8305 (5)	0.4790 (5)	0.0467 (12)
C3	−0.0607 (10)	0.8401 (5)	0.3865 (5)	0.0562 (14)
H3	−0.0557	0.7679	0.3559	0.067*
C4	−0.2109 (10)	0.9584 (5)	0.3386 (5)	0.0541 (14)
H4	−0.3058	0.9637	0.2767	0.065*
C5	0.0752 (9)	0.9387 (5)	0.5243 (4)	0.0440 (12)
C6	0.2199 (9)	0.9345 (5)	0.6184 (5)	0.0482 (13)
C7	0.3779 (10)	0.8079 (5)	0.6691 (5)	0.0523 (14)
C8	0.4892 (9)	0.5658 (5)	0.6912 (5)	0.0537 (14)
H8A	0.6355	0.5891	0.7224	0.064*
H8B	0.5580	0.5257	0.6292	0.064*
C9	0.2958 (10)	0.4562 (6)	0.8023 (5)	0.0544 (14)
C10	0.4188 (10)	0.3238 (5)	0.8827 (5)	0.0550 (14)
C11	0.2281 (13)	0.2022 (6)	0.9871 (6)	0.0676 (16)

	U11	U22	U33	U12	U13	U23
F1	0.061 (2)	0.082 (2)	0.086 (2)	−0.0057 (16)	−0.0279 (18)	−0.0114 (19)
F2	0.091 (2)	0.063 (2)	0.074 (2)	0.0213 (17)	0.0167 (18)	−0.0222 (18)
F3	0.074 (2)	0.098 (3)	0.083 (3)	−0.0005 (18)	−0.0340 (18)	−0.021 (2)
F4	0.108 (3)	0.077 (2)	0.070 (2)	0.0396 (19)	−0.0012 (19)	−0.0278 (19)
F5	0.107 (3)	0.071 (2)	0.078 (2)	0.025 (2)	−0.018 (2)	−0.0064 (19)
F6	0.101 (3)	0.087 (3)	0.082 (3)	0.023 (2)	0.026 (2)	−0.007 (2)
F7	0.147 (4)	0.081 (3)	0.125 (4)	−0.039 (3)	−0.057 (3)	−0.008 (3)
O1	0.095 (3)	0.070 (3)	0.073 (3)	0.031 (2)	−0.024 (2)	−0.042 (2)
O2	0.079 (3)	0.067 (3)	0.080 (3)	0.0131 (19)	−0.038 (2)	−0.029 (2)
N1	0.054 (2)	0.040 (2)	0.051 (3)	0.0061 (18)	−0.010 (2)	−0.018 (2)
C1	0.059 (3)	0.046 (3)	0.052 (3)	0.009 (3)	−0.006 (3)	−0.021 (3)
C2	0.049 (3)	0.048 (3)	0.044 (3)	0.003 (2)	−0.002 (2)	−0.023 (3)
C3	0.068 (3)	0.051 (3)	0.057 (3)	0.006 (3)	−0.015 (3)	−0.028 (3)
C4	0.064 (3)	0.058 (3)	0.047 (3)	0.005 (3)	−0.016 (2)	−0.026 (3)
C5	0.045 (3)	0.044 (3)	0.038 (3)	0.001 (2)	−0.002 (2)	−0.014 (2)
C6	0.046 (3)	0.051 (3)	0.041 (3)	0.003 (2)	−0.003 (2)	−0.014 (3)
C7	0.051 (3)	0.052 (3)	0.044 (3)	0.000 (2)	−0.004 (3)	−0.012 (3)
C8	0.050 (3)	0.055 (3)	0.051 (3)	0.009 (2)	−0.010 (2)	−0.017 (3)
C9	0.053 (3)	0.056 (3)	0.057 (4)	0.010 (3)	−0.010 (3)	−0.026 (3)
C10	0.060 (3)	0.058 (3)	0.054 (3)	0.014 (3)	−0.011 (3)	−0.031 (3)
C11	0.085 (4)	0.056 (4)	0.058 (4)	0.003 (3)	−0.024 (4)	−0.015 (3)

F1—C9	1.357 (6)	C2—C5	1.389 (6)
F2—C9	1.341 (6)	C3—C4	1.402 (7)
F3—C10	1.325 (6)	C3—H3	0.9300
F4—C10	1.338 (6)	C4—C6i	1.360 (7)
F5—C11	1.321 (6)	C4—H4	0.9300
F6—C11	1.294 (7)	C5—C6	1.425 (6)
F7—C11	1.314 (6)	C5—C5i	1.435 (9)
O1—C1	1.213 (6)	C6—C4i	1.360 (7)
O2—C7	1.223 (6)	C6—C7	1.491 (7)
N1—C7	1.387 (6)	C8—C9	1.522 (7)
N1—C1	1.398 (6)	C8—H8A	0.9700
N1—C8	1.467 (6)	C8—H8B	0.9700
C1—C2	1.477 (7)	C9—C10	1.513 (7)
C2—C3	1.380 (7)	C10—C11	1.539 (8)
C7—N1—C1	124.8 (4)	N1—C8—C9	109.7 (4)
C7—N1—C8	117.3 (5)	N1—C8—H8A	109.7
C1—N1—C8	117.8 (4)	C9—C8—H8A	109.7
O1—C1—N1	120.4 (5)	N1—C8—H8B	109.7
O1—C1—C2	123.0 (5)	C9—C8—H8B	109.7
N1—C1—C2	116.6 (5)	H8A—C8—H8B	108.2
C3—C2—C5	120.2 (5)	F2—C9—F1	105.5 (4)
C3—C2—C1	119.6 (5)	F2—C9—C10	108.6 (4)
C5—C2—C1	120.2 (5)	F1—C9—C10	108.7 (4)
C2—C3—C4	120.1 (5)	F2—C9—C8	110.1 (4)
C2—C3—H3	119.9	F1—C9—C8	109.2 (4)
C4—C3—H3	119.9	C10—C9—C8	114.3 (4)
C6i—C4—C3	120.9 (5)	F3—C10—F4	107.7 (4)
C6i—C4—H4	119.6	F3—C10—C9	109.0 (4)
C3—C4—H4	119.6	F4—C10—C9	108.5 (4)
C2—C5—C6	122.3 (5)	F3—C10—C11	107.7 (5)
C2—C5—C5i	120.6 (6)	F4—C10—C11	107.2 (5)
C6—C5—C5i	117.2 (6)	C9—C10—C11	116.4 (5)
C4i—C6—C5	121.0 (5)	F6—C11—F7	109.6 (6)
C4i—C6—C7	121.4 (5)	F6—C11—F5	108.2 (5)
C5—C6—C7	117.7 (5)	F7—C11—F5	107.3 (5)
O2—C7—N1	121.5 (5)	F6—C11—C10	111.6 (5)
O2—C7—C6	120.7 (5)	F7—C11—C10	110.2 (5)
N1—C7—C6	117.8 (5)	F5—C11—C10	109.8 (5)
C7—N1—C1—O1	171.2 (4)	C4i—C6—C7—N1	173.8 (4)
C8—N1—C1—O1	−4.5 (7)	C5—C6—C7—N1	−5.4 (6)
C7—N1—C1—C2	−9.8 (7)	C7—N1—C8—C9	95.1 (5)
C8—N1—C1—C2	174.5 (4)	C1—N1—C8—C9	−88.9 (5)
O1—C1—C2—C3	2.8 (8)	N1—C8—C9—F2	−50.4 (6)
N1—C1—C2—C3	−176.1 (4)	N1—C8—C9—F1	65.0 (6)
O1—C1—C2—C5	−178.0 (5)	N1—C8—C9—C10	−173.0 (5)
N1—C1—C2—C5	3.1 (7)	F2—C9—C10—F3	−59.0 (5)
C5—C2—C3—C4	−0.6 (7)	F1—C9—C10—F3	−173.3 (4)
C1—C2—C3—C4	178.6 (4)	C8—C9—C10—F3	64.4 (6)
C2—C3—C4—C6i	0.4 (8)	F2—C9—C10—F4	−176.0 (4)
C3—C2—C5—C6	−179.1 (4)	F1—C9—C10—F4	69.7 (5)
C1—C2—C5—C6	1.7 (7)	C8—C9—C10—F4	−52.6 (6)
C3—C2—C5—C5i	0.0 (8)	F2—C9—C10—C11	63.0 (6)
C1—C2—C5—C5i	−179.2 (5)	F1—C9—C10—C11	−51.3 (7)
C2—C5—C6—C4i	−179.8 (4)	C8—C9—C10—C11	−173.5 (5)
C5i—C5—C6—C4i	1.1 (8)	F3—C10—C11—F6	65.9 (6)
C2—C5—C6—C7	−0.6 (7)	F4—C10—C11—F6	−178.4 (5)
C5i—C5—C6—C7	−179.7 (5)	C9—C10—C11—F6	−56.8 (7)
C1—N1—C7—O2	−169.7 (5)	F3—C10—C11—F7	−172.1 (5)
C8—N1—C7—O2	6.0 (7)	F4—C10—C11—F7	−56.4 (6)
C1—N1—C7—C6	11.0 (7)	C9—C10—C11—F7	65.2 (7)
C8—N1—C7—C6	−173.3 (4)	F3—C10—C11—F5	−54.1 (7)
C4i—C6—C7—O2	−5.5 (7)	F4—C10—C11—F5	61.6 (6)
C5—C6—C7—O2	175.3 (4)	C9—C10—C11—F5	−176.8 (5)